Phosphorus oxychloride → Ecgonine

HRID 1604009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1604009
CN1C2C(C(O)=O)=CCC1CC2.[CH3:13][N:14]1[C@H:18]2[C@@H:19]([C:31]([O:33]C)=[O:32])[C@@H:20]([O:22]C(C3C=CC=CC=3)=O)[CH2:21][C@@H:15]1[CH2:16][CH2:17]2.P(Cl)(Cl)(Cl)=O>Cl>[CH3:13][N:14]1[C@H:18]2[C@@H:19]([C:31]([OH:33])=[O:32])[C@@H:20]([OH:22])[CH2:21][C@@H:15]1[CH2:16][CH2:17]2

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 101709(1R)-8-Methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylic acidHCID 446220Cocaine2×

Produkt 1

HCID 91460Ecgonine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

In later references Anhydroecgonine and esters thereof have been prepared by hydrolysis of cocaine in aqueous hydrochloric acid followed by dehydration with phosphorus oxychloride (J. Amer. Chem. Soc., 82 (1960), page 4643 and EP-A1-604 355 ). Although both the hydrolysis of cocaine and the dehydration of ecgonine produces high yields, it is a serious drawback to this method that the reaction mixture becomes syrupy during the dehydration step which makes stirring almost impossible. Using SOCl2 as dehydrating agent causes similar problems.

Quellen und Nachweise

ORD-Eintrag
ord-0b0afd82917d41c289a2c5d583fb1261
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05990312

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